


Magnificent Mile

by compo67



Series: Chicago Verse [10]
Category: Supernatural
Genre: Anal Sex, Bottom Sam, Consent, Domestic, Episode Related, Explicit Sexual Content, Fingerfucking, M/M, Oral Sex, POV Sam Winchester, Schmoop, Top Dean, looking back
Language: English
Status: Completed
Published: 2013-10-02
Updated: 2013-10-02
Packaged: 2017-12-28 06:00:52
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,285
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/988555
Author URL: https://archiveofourown.org/users/compo67/pseuds/compo67
Summary: <blockquote class="userstuff">
              <p>References to the Episode 2x17 "Heart" and part of the Chicago Verse. Sam looks back at what happened between him and Madison, and between him and Dean shortly after.</p>
            </blockquote>





	Magnificent Mile

**Author's Note:**

> This is a specific prompt given to me, which I asked for and was super happy to fill. The request was for healing moments and sex between the boys right after "Heart." I tied it into the Chicago Verse because I think of Sam as one of those guys who gets caught up in reflection a lot. 
> 
> I also love older!Dean. XD
> 
> Comments, kudos, etc. are greatly appreciated! 
> 
> (You don't have to read the rest of Chicago Verse to understand this, but it would probably help.)

At forty-five years old, waiting in the lobby of a physical therapist’s office, Sam was reading a magazine. He can’t even remember what it was that he had been reading, only that it had been something generic. Like a Reader’s Digest or Time probably. He’d swung by after work since it was near a pink line stop and he knew there would be nagging if he didn’t. Always with the nagging.

The intake nurse recognized him and got him a glass of water.

Bored, he flipped a page.

Then there it was. Something so ordinary, in the most common of places. Just another magazine ad.

He remembered what he’d said to her.

It seemed so ridiculous at the time, too. But looking back it seemed just the thing any awkward, insecure, slightly grieving young man would say to an attractive, slightly intimidating young woman.

“You’re unusual.”

And there she was, unusual again, with that confident, radiant smile.

Well, at least someone who looked like her was. The resemblance was extraordinary. If… events…it could very well be her, had things turned out differently.

The temptation to rip that page out of the magazine was strong, but he hesitated. His fingers smoothed out the page, circled near the woman’s long brown hair. Everyone had been so young and inexperienced then, even the Winchester boys who had by that time earned their guns. Forty-five was by no means old, but Sam felt so different. There was something about being older that counted for something.

How many people’s last breaths had been in his presence?

How many people had Sam Winchester’s face as their last and final vision before passing?

He’d written that down once, in a half dazed state the year before they settled down and they were passing through another motel on their way to another hunt.  Of course the list had been torn from his hands and burned, but even if the ink was destroyed that didn’t mean the facts were.

She’d been his first because he’d liked her spirit, that independence. The fact that she challenged him in all ways and by the end of it, she’d fallen asleep on his arm.

His past and her past were never mentioned completely. It wasn’t like that; they hadn’t been like that. And foolishly, he thought they could start there and build something more stable. Sam smiled to himself and closed the magazine, set it aside on the coffee table. He’d been led down that road so many times with so many people. Every time he thought—he took a chance—that they could survive together, face the world and each other together, it always led to something twisted and wrong.

In whatever great book of fate, she hadn’t been meant to die that way. Not like that.

The nurse lets Sam know the appointment is nearly done—do they want crutches or a chair?

Dazed, Sam weakly replied that crutches will be fine.

He was having a small breakdown in the waiting room and he has to put himself together in fifteen minutes or less, preferably less.

There were some hunters who probably wouldn’t have had any trouble doing what he did. And there were some hunters who probably would have taken the gun from him and did it themselves because hesitance meant weakness.

It took weeks for him to return to the state he’d been prior, which really, wasn’t much of an improvement. Instead of negative, he reached zero and plateaued.

The offer had been there before and Sam hadn’t wanted to take it.

Well, okay, he took it. Right after Jess, he took it. Both of them were drunk and desperate and drifting. It made sense. But he didn’t want to talk about it or acknowledge it or do it again. What was the point of starting things back up only to discover that there was someone like Cassie, that there would _always_ be Jess, and of course, there was John.

So when Madison walked into his life—let him into her house and into her bed—there was a glimpse of something there. Something that could last longer than a motel fuck or a two week stay.

He wondered what she would think of him now.

Daytime television never really caught on with him but every time there was laundry to fold he thought of her. Thinking though, was different than seeing.

“Mr. Winchester?” the nurse again, trying to get his attention.

“Yeah? Sorry,” he muttered and stood up, walking over to her desk. “He ready?”

“Ah, not quite. Seems that he had… an altercation with Smith again.”

“Again?” Sam sighed and rubbed his temples. “How bad?”

Her expression didn’t bode well. She did her own sigh and gave him an estimate of ten more minutes. Sam sat back down but didn’t pick up the same magazine. Instead, he pulled his suitcase onto his lap and opened it, lifting up all the papers and folders he had stuffed inside it. On the bottom was something like a security blanket. It probably didn’t seem like much, but Winchesters always had their own values.

It looked like an innocent piece of fabric.

When Sam finally broke down—right after they dodged the FBI after their fake stint in prison—Dean took him to a hotel. Not a motel. An actual with-a-bell-hop-hotel that had families and old people staying in them instead of truckers and drifters like themselves. It was charged to one of their many fake credit cards but Dean hadn’t spared any expense. He took a snotty, cranky, depressed Sam and hauled him up to the room. It wasn’t a penthouse suite exactly, but it was also very swank compared to what they were used to. There were no visible stains anywhere and the room smelled clean. The bathroom had actual towels and Sam was for once not afraid to touch anything.

Sniffling and grunting that this was different, Sam threw himself onto the single king bed in the room.

Wait.

He looked at Dean, feeling his entire body tense up. Dean looked back, his face open and honest.

“Offer’s still there,” Dean murmured, fiddling with his pocketknife. “But they got a fold out couch in here too and you know… I’d be jus’ fine with that.”

In an abnormal environment, surrounded by things that mimicked a home, Sam accepted the offer.

And what he got in return was entirely unexpected.

He thought they’d fumble around like before, maybe Dean would break out a hidden bottle of tequila and they’d get smashed and then they’d maybe get to humping each other in a pile of frustration and want. Or maybe it would be like the very first time they crossed that line, dark and quiet and seemingly swept away easily.

So when Dean kept the lights on and there was no alcohol involved as they awkwardly found a rhythm again, Sam could barely breathe or understand just what was going on. He tried not to think about it too much because if he did it would consume him. But who was he trying to fool? They were rough with each other but in a gentler way and that didn’t make any sense. Both of them fought for control of their pace but in the end Sam gave way. He wanted to see where it would go.

They never were much about talking whenever they’d managed to sneak blow jobs and muffled sex wherever they were when they were teenagers. Yeah, Dean liked to murmur filthy things and egg Sam on, especially when Sam was blowing him, but true actual talking during sex wasn’t their style. And that’s not what this was like either.

Silent and studious, Dean impatiently undressed them until their cocks were hanging heavy, bobbing whenever either one moved. As Dean ground them together, he also pushed and pressed his mouth against Sam’s. They had contact from head to toe.

“Sammy,” Dean had whispered. “Please.”

One, two, three breaths.

What was the point of doing this? There would always be another town with another girl for Dean to hit on and spend the night with instead of coming back to Sam. There would always be another corner Sam would turn and smack right into his grief instead of asking for help and coming back to Dean.

Right?

“Yeah Dean, yeah.”

He expected the fucking to start so when it didn’t, he snorted in surprise. There was a lazy, sloppy, wet blow job from Dean’s god damned mouth, with a smirk at the end of it. And then, just minutes after, there was a languid make out session where Sam didn’t call Dean gross or unsanitary. When Sam got hard again, they didn’t stop kissing. When Sam could barely breathe or put together sentences, they didn’t stop kissing. Dean’s tongue was insistent and warm, familiar and clever. The kisses moved from his mouth to his jawline to his neck to his collarbone. Two marks were roughly given but tenderly soothed afterwards with a few slow licks.

Unhurried, Dean prepped him.

It’d been a while for both of them this way. And while many people liked to focus on Dean’s mouth, Sam knew that the man’s hands were a tie for best feature. They were hands that were tough and strong but elegant and deft.  They were reverent and respectful of all the ways Sam wanted to be touched and didn’t want to be reminded.

One finger plus lube plus constant, deep kissing.

Two fingers plus Dean’s free hand tightly gripping a handful of Sam’s hair.

Three fingers plus holding their mouths close together, breathing in each other’s pants and huffs for air.

Sam was worked open slow and thorough, so that when Dean finally pushed in, it was smooth and familiar. At first, Dean pushed Sam’s legs up to his chest and thrust in that way. However, not too long after, Sam initiated a switch.

He nearly had to beg for the change; he insisted he was okay, he wanted it.

Holding onto the headboard, on his knees, he pushed himself back, where Dean’s hips perfectly met his.

Although Sam tried to get Dean to be rougher, Dean didn’t give in. He fucked in and out of Sam in a deep, steady rhythm, his cock twitching every time Sam either flipped his hair over his shoulder or Dean gripped onto a handful and pulled.

The base of his cock was gripped and his orgasm was delayed twice.

About to knock Dean off of him, Dean started to pick up the pace. Finally, Sam was hearing the tell-tale sounds of them fucking, noises that had always been distinct to them: the headboard banging against the wall, the mattress creaking with every snap of Dean’s hips, the sound of Dean’s heavy, firm balls slapping against Sam’s hips, the squelch and slick of lube, the little huffing sounds Dean made whenever Sam clenched his ass. Sober, he was able to think about all of this. Being fucked by Dean was different than sleeping with someone else. It felt like relapsing into something Sam didn’t want to think about or face or question or even know of its existence. Not now. Not yet.

Despite all of his rough movements and a few wrong angles now and then, Dean remained sincere in his touches. One hand went from Sam’s hair to his shoulders, to his back, to his legs, and Sam realized that Dean was touching just for the sake of touching. When one hand appeared on Sam’s cheek, cradling his face for the briefest of moments before returning to pull at his hair, Sam almost lost it in every way possible. It wasn’t fair that someone so damaged could break him and piece him back together. It wasn’t fair that Dean got to see all of what broke Sam and Sam never got to see what broke Dean.

He was pretty upset with life and everything about their lives in particular at that point.

And how no matter how worldly Sam could be, his older brother always seemed to be able to wedge himself into Sam’s perspective, taking up his entire point of view.

Of course Dean noticed Sam was thinking too much, so he pushed them both flat onto the bed and fucked Sam in long, deep strokes, intentionally not hitting his prostate. When Sam was about to complain, he felt careful fingers slide up his inner thigh. With a gasp, he felt a finger slide in beside Dean’s cock. He groaned when he felt Dean push in all the way, fully in, with two fingers in addition.

This was new. And weird. But mostly just odd.

He heard Dean grunt and felt Dean’s hips stutter, like he was holding back. Eventually, he started moving in slow circles, counterclockwise, hitting Sam’s prostate every time he reached noon. It was slow enough that Sam could feel Dean’s fingers moving in rhythm.

It was like his brother was trying to crawl inside him in any way possible.

Pressed chest to back, both their legs spread, and with one, two, three firm thrusts directly on his prostate, Sam let go.

“Coming, coming,” Sam warned, shutting his eyes tight, back arching. Every muscle in his body wound up tight under Dean’s. His cock shot three, four, five long strips of come, just enough to coat his lower belly and the unfortunate bed underneath him. He groaned as he felt each twitch of his cock and Dean’s. Satisfied that Sam had come, Dean kept his pace and grunted as his warning. He bit onto Sam’s right ear lobe and breathed hard. Sam could see how tight Dean was holding onto the bed.

His brother came inside him without a condom because that’s what they had done since the very first time. Because Sam trusted Dean in that aspect. He also trusted Dean to pull out carefully, because it hurt if he didn’t—they’d found that out multiple times when John had come back to the motel room because he’d forgotten something. Sighing, Sam felt Dean slip out.

Sam was flipped over suddenly and barely had any time to brace himself for Dean’s mouth on his cock. His first reaction was to push his hips up, towards that fucking mouth, and his second was to spread his legs without even being asked or told. This is when he knew there would be no stopping this. That whatever happened to either of them, there would always be _this_.

And he wasn’t sure how to feel about that.

He didn’t have all the answers or assurance when he was in his twenties. It took years to sort out all his emotions about Dean and _this_. They could have sex one night and argue the next hour. They were never exclusive and maybe… it wasn’t a bad thing. Because they both learned from other people.

It was never a straightforward, clear as day fact to Sam that he would end up here, in the waiting room of the physical therapist’s office, forty-five and settled. Fucking settled. There was a house (a home), a tiny yard, a watchful neighbor, a community that they belonged to.

He’d taken a piece of that hotel blanket.

Cut out a patch with his pocketknife.

Did it a few hours after Dean had blown him while fucking him with his fingers, messing with his own come, licking at it a few times. He’d blown Sam like it was something they did every day. And after that it practically was.

His brother wasn’t the best person to go to for talking about feelings or grief. Most of the time Dean wanted to crack ridiculous jokes and swagger about, reckless and young.

But something had to be said about the man’s ability to touch.

How careful and thoughtful each touch was, even when it was with his fingers scissoring Sam open, twisting and curling and hitting his prostate until Sam cried out and shot into his brother’s talented throat.

How attentive he was to get a warm, wet rag and clean Sam up without Sam ever having to ask.

How Dean didn’t sleep at all that night but Sam did, deep and restful.

 

“Mr. Winchester? He’s on his way.”

Jolted to the present, Sam let out a deep breath. Damn, he was getting old. He was getting lost in his own memories, swimming around in grief and confusion like it was his job.

He tucked away the piece of fabric, back into its home inside his briefcase, then stood up. When the door to the waiting room opened, he moved forward a few steps, ready to help, but eased off when he saw the look on Dean’s face.

“God damned doctors don’t know fuck all,” Dean snapped, moving forward slowly on crutches. “I tell ‘em it hurts and what the fuck do they do?! Ten more reps! Don’t look at me that way you fucker,” Dean growled at Sam. “Why didn’t you get me a chair? Huh? Thought I might like to be in more pain after my session with fuck face?”

Rolling his eyes, Sam sighs. “Dean, could you tone down your language?” They were the only ones in the waiting room thankfully, but Sam was sure the entire staff could hear them. The receptionist sure could. As Dean grumbled on about how he earned the right to swear as often as he fucking pleased, Sam asked for a wheelchair, which was brought out so fast it should have been a surprise. Wheeling out of the office and towards the elevator so they could leave in a cab, Sam asked Dean how the rest of the appointment went. Dean shrugged and grunted.

It was his left knee giving him problems; had been for years, even if Dean refused to talk about it. Finally, after one surgery and three weeks of intensive PT, they were down to a once a week appointment. Though Sam thought the staff didn’t get paid enough to deal with his brother.

Once they reached outside, Sam gave Dean his briefcase to hold while he hailed a cab.

At home, in their tiny living room, Sam perched Dean on his favorite couch and grabbed the usual supplies: a heating pad, three pillows, and the remote.

“I’ll make dinner,” Sam announced, flipping through the mail, setting Dean’s aside. “Chicken okay?”

“The fuck is wrong with you?” Dean demanded to know, twisting as much as he could to look at Sam.

“Well, you’re acting like a five year old who cusses a lot,” Sam replied, curtly. “They’re gonna kick us out of that place if you’re not careful.”

Dean only smirked. “Nah, Sammy, the big boss there likes me. Wants a piece of this.”

“No one wants a piece of your old ass,” Sam bantered back. “Except this one guy I know but he doesn’t have good taste.”

With a snort, Dean waved him away. They talked from the living room and the kitchen without a problem, their house was that small.

“Sammy, what’s the deal? You gonna tell me or do I have to kick it out of you?”

“You couldn’t kick anything out of a piñata right now, dude.”

“Fuck you. Show some respect. C’mon, I’m not playing this game.”

Putting together dinner, Sam smiled to himself. Once everything was cooking, he’d go into the living room and massage the leftover tension out of Dean’s left leg. He’d give him a kiss and hope it would turn into something more, whatever either of them wanted. Because that was their life now: whatever they wanted.

 

And wasn’t it funny.

Whatever they wanted turned out to be this, here, together.


End file.
